WO2010070237 Derivatives of 6-cycloamino-2-thienyl-3-(pyridin-4-yl)imidazo[1,2-B]-pyridazine and 6-cycloamino-2-furanyl-3-(pyridin-4-yl)imidazo[1,2-B]-pyridazine, preparation and therapeutic applicati

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Biological target:

Casein kinase 1: CK1



Steps Conditions Reactions
a 1-piperazinecarboxaldehyde, 140oC, 5h, then HCl 4N, 80oC, 2h SnAr
b Boc2O, Et3N, THF, 0 oC Secondary amine protection (Boc-protection)
c Butanol 100oC Imidazopyridazine formation
d Ethyl chloroformate, pyridine, 0oC
e ortho-Chloranil, toluene, 1h   Aromatisation
f   TFA/CH2Cl2 (0.6/10), 0oC, 2h Secondary amine formation (Boc-deprotection)
Steps Conditions Reactions
a NIS, CH3CN, 60oC Iodation
b Cs2CO3, (PdCl2(dppf).CH2Cl2), THF-H2O 9/1 Suzuki coupling reaction
c DIEA, Pentanol, 150oC, 24h SnAr